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Extracellular chromone derivatives in cell cultures of Pimpinella anisum. Influence of elicitation with methyl jasmonate and 2β-methyl cyclodextrins

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Abstract

Objectives

To explore the potentiality of undifferentiated Pimpinella anisum L. cell cultures for the production of secondary metabolites by means of elicitation.

Results

Two chromone compounds were secreted to the medium of undifferentiated cultures of P. anisum: 4-methoxyfuro[3,2-g]chromen-7-one, known as bergapten, which is constitutive to anise, and 5-hydroxy-7-methoxy-2-methylchromen-4-one, the rare chromone eugenin, not yet described in P. anisum. Caffeoyl quinic acid species were also identified in the biomass. Elicitation with methyl jasmonate enhanced chromone accumulation in the medium and stimulated phenolic acid metabolism in the biomass (11 mg caffeoyl quinic acids g−1 DW cells). The application of 2,6-dimethyl-β-cyclodextrins to cultures led to an intense accumulation of chromones, with nearly 10 mg l−1 bergapten and 150 mg l−1 eugenin being accumulated extracellularly after optimal elicitation conditions.

Conclusions

The significant amounts of eugenin obtained in the anise cultures and the stability of production over long periods of time can be of interest for its biotechnological production and for future studies on biosynthesis regulation.

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References

  • Almagro L, Perez AJ, Pedreño MA (2011) New method to enhance ajmalicine production in Catharanthus roseus cell cultures based on the use of cyclodextrins. Biotechnol Lett 33:381–385

    Article  CAS  PubMed  Google Scholar 

  • Bourgaud F, Hehn A, Larbat R, Doerper S, Gontier E, Kellner S, Matern U (2006) Biosynthesis of coumarins in plants: a major pathway still to be unravelled for cytochrome P450 enzymes. Phytochem Rev 5:293–308

    Article  CAS  Google Scholar 

  • Chang LW, Chiu LW, Lai JH, Lin HC (2003) Immunosuppressive flavones and lignans from Bupleurum scorzonerifolium. Phytochemistry 64:1375–1379

    Article  CAS  PubMed  Google Scholar 

  • Czepa A, Hofmann T (2003) Structural and sensory characterization of compounds contributing to the bitter off-taste of carrots (Daucus carota L.) and carrot puree. J Agric Food Chem 51:3865–3873

    Article  CAS  PubMed  Google Scholar 

  • Ernst D (1989) Pimpinella anisum L. Anise: cell culture, somatic embryogenesis, and the production of anise oil. In: Bajaj YPS (ed) Biotechnology in agricultures and forestry, vol 1. Medicinal and aromatic plants II. Springer, Berlin, pp 381–387

    Google Scholar 

  • Ishikawa A, Kitamura Y, Ozeki Y, Ito Y, Yamada A, Watanabe M (2005) Post-stress metabolism involves umbelliferone production in anthocyanin-producing and non-producing cells of Glehnia littoralis suspension cultures. J Plant Physiol 162:703–710

    Article  CAS  PubMed  Google Scholar 

  • Klausmeyer P, Zhou Q, Scudiero DA, Uranchimeg B, Melillo G, Cardellina JH, Shoemaker RH, Cahng CJ, McCloud TG (2009) Cytotoxic and HIF-1alpha inhibitory compounds from Crossosoma bigelovii. J Nat Prod 72:805–812

    Article  CAS  PubMed  Google Scholar 

  • Komaraiah P, Reddy GV, Reddy PS, Raghavendra AS, Ramakrishna SV, Reddanna P (2003) Enhanced production of antimicrobial sesquiterpenes and lipoxygenase metabolites in elicitor-treated hairy root cultures of Solanum tuberosum. Biotechnol Lett 25:593–597

    Article  CAS  PubMed  Google Scholar 

  • Leonti M, Cabras S, Weckerle CS, Solinas MN, Casu L (2010) The causal dependence of present plant knowledge on herbals—contemporary medicinal plant use in Campania (Italy) compared to Matthioli (1568). J Ethnopharmacol 130:379–391

    Article  PubMed  Google Scholar 

  • Murashige T, Skoog F (1962) A revised medium for rapid growth and bioassay with tobacco tissue cultures. Physiol Plant 15:473–497

    Article  CAS  Google Scholar 

  • Ramirez-Estrada K, Vidal-Limon H, Hidalgo D, Moyano E, Golenioswki M, Cusidó RM, Palazon J (2016) Elicitation, an effective strategy for the biotechnological production of bioactive high-added value compounds in plant cell factories. Molecules 21:182

    Article  PubMed  Google Scholar 

  • Reichling J, Merkel B (1993) Induced formation of coumarin derivatives in suspension cultures of Pimpinella anisum. Planta Med 59:187–188

    Article  CAS  Google Scholar 

  • Shojaii A, Fard MA (2012) Review of pharmacological properties and chemical constituents of Pimpinella anisum. SRN Pharm. https://doi.org/10.5402/2012/510795

    Google Scholar 

  • Vickery ML, Vickery B (1981) Secondary plant metabolism. Macmillan, London

    Book  Google Scholar 

  • Widholm JM (1972) The use of fluorescein diacetate and phenosafranine for determining viability of cultured plant cells. Stain Technol 47:189–194

    Article  CAS  PubMed  Google Scholar 

Download references

Acknowledgements

This work has been supported by the Spanish Ministry of Science and Innovation (BIO2014-51861-R).

Supporting Information

Supplementary Fig. 1—Chromatograms acquired at A257 from fruit extracts (a), pure anethole (b) and cultures (medium extracts, c and biomass, d)

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Correspondence to Purificación Corchete.

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10529_2017_2482_MOESM1_ESM.pptx

Supplementary Fig. 1 Chromatograms acquired at A257 from fruit extracts (a), pure anethole (b) and cultures (medium extracts, c and biomass, d) (PPTX 267 kb)

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Soto-Argel, C., Hidalgo, D., Palazon, J. et al. Extracellular chromone derivatives in cell cultures of Pimpinella anisum. Influence of elicitation with methyl jasmonate and 2β-methyl cyclodextrins. Biotechnol Lett 40, 413–418 (2018). https://doi.org/10.1007/s10529-017-2482-3

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  • DOI: https://doi.org/10.1007/s10529-017-2482-3

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